Triacetoxyperiodinane → HCID 76659872, compound

HRID 884396Notes

Reaction equation

HRID 884396 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:13][OH:14])[CH:10]2[O:15][CH2:16][C:17]([O:20][CH3:21])([O:18][CH3:19])[CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH:13]=[O:14])[CH:10]2[O:15][CH2:16][C:17]([O:20][CH3:21])([O:18][CH3:19])[CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66921021HCID 66921021, compound

Product 1

HCID 76659872HCID 76659872, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol 1g (370 mg, 1.22 mmol) dissolved in dry DCM (10 mL) was added Dess Martin periodinane (673 mg, 1.59 mmol). The reaction was stirred for 40 minutes and then quenched by addition of 10 mL of 10% Na2S2O3:NaHCO3(sat) 1:1. The solution was diluted with DCM (50 mL) and extracted with a 1:1 mixture of 10% Na2S2O3:NaHCO3(sat) (50 mL). The organic phase was dried with Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography (heptane: ethyl acetate (2:1) which gave the title compound (290 mg, 79%).

Workup

  1. customquenched by addition of 10 mL of 10% Na2S2O3:NaHCO3(sat) 1:1
  2. additionThe solution was diluted with DCM (50 mL)
  3. extractionextracted with a 1:1 mixture of 10% Na2S2O3
  4. dry with materialThe organic phase was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (heptane: ethyl acetate (2:1) which

Sources & evidence

ORD record
ord-f859f92f64404efdb80be678d56296df
Source dataset
uspto-grants-2012_08
Patent number
US08242119B2

Reaction notes

Loading…